Don't. Do. What. I. Did.

A former pro skier breaks down the lessons learned from two failed businesses.

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Entrepreneur Leadership Network Contributor
CEO of The Media House, Co-Founder of Health Media Group
5 min read
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I approached my journey into private enterprise the way I did my professional skiing career: dissecting what the best-of-the-best did in order to gain insights. I sought out face time with people like Tim Ferriss and Seth Godin while becoming a student of the industry itself. 

The qualities required to be a world-class athlete I assumed were necessary for any type of success. But the will to succeed in sports also blinded me as I entered this next chapter in my life. 

I’ve started multiple businesses in the past five years: An online ski school, an ecommerce store, a marketing agency that has brought me the bulk of income...and then there’s my graveyard of less notable attempts. 

Herein lies the lessons learned via my initial, and less-than-stellar, endeavors... 

Related: Dear Brit: 'I'm Freaked Out by Failure!'

1. Know your biases

Willpower stems from a bias. It's an unconscious tendency to overestimate our capability to accomplish any task.

For me, it led to an inability to see that I didn’t have a product-market fit with my first business until I had invested a large portion of my capital, time and energy into something that wasn’t viable. I refused to believe it and continued to push forward.

My second mistake was the sunk cost fallacy. I figured that because I'd invested a large amount of my time, money and energy? I wouldn’t take "no" for an answer. If I just tried harder? I’d succeed. 

My biases blinded me as I continued to invest in a product that didn’t have viability. I got too attached to my initial idea instead of reworking a business that would actually add value to the market. 

Quickly identify your biases so you can hedge against them. Gary Vaynerchuk, former Belorussian wine critic and current multimillionaire digital marketing guru, often speaks of self-awareness being the key to success. Seek counsel from seasoned veterans that will help you refine your ideas to avoid self-imposed pitfalls. 

2. Test assumptions

I still believe there are millions of companies, within the United States alone, that need better-designed websites.

But instead of relying on my then vague assumptions, I should have focused on the real numbers: How many businesses are there in the U.S.? How many, on average, have a decent site? How many have enough money for the type of URLs I design? How many are going to actively search for someone to help them with their domain? 

When you test each assumption individually you give yourself a chance to parse out data and understand the market before letting your biases drive you to make questionable decisions. I found myself stringing together a list of presupposed guesses that “had to be true” in order to create a belief that I could do it.

If I had gained insight with a data-driven approach, I would have actually enjoyed the process, instead of constantly hushing the questioning voices within my head due to delusions of grandeur. 

When I started looking at business as a series of hypotheses to be tested scientifically, I learned a lot about how to embrace failure and move on from my many mistakes.

Related: Why Failure is Necessary in Order to Succeed as an Entrepreneur

3. The more you rush, the longer it takes

Early on I wanted things to manifest in unrealistic timelines and it plagued my ability to produce tangible results. That sense of urgency made me too confident in my idea and that it could happen on the fly. 

After having success breaking onto the Freeskiing World Tour, I lived under the allusion that my athletic trajectory could easily be reproduced in the world of business. This was in large portion due to my overconfidence. 

I set extremely unrealistic expectations for myself. It seemed to work on the slopes, so I assumed it would work with a start-up. Unfortunately, it just slowed down my progress and created friction in moving towards the end goal. 

Rushing the hiring process of outside agencies (or inside employees) can be deadly. Do your due diligence in whichever route you choose while understanding you can’t speed the process.

4. One strong product beats all-in-one solutions

When I first changed careers, I didn’t understand that once you have a happy customer base it’s much easier to expand laterally. The keyword being "happy". This is why you hear so much about niching down. It’s more important to have one repeatable system that generates satisfied customers than it is to have “boutique” solutions for each patron. 

Advice like “say yes and learn how to do it later” is a dangerous prospect to live by depending on your level of competency. Learning to niche down is one of the hardest things to do as an entrepreneur. 

I used to question whether I should take a project on and still saying "yes", regardless. It led toa lot of late nights, stress and barely satisfied customers. Lately, I’ve found that limiting my service offering to one repeatable system is the most effective decision I can make. 

Related: Failure to Pivot Can Lead Your Startup to Death

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